PL200868B1 - Sposób wytwarzania 1,14-węglanu 14ß-hydroksy-10-deacetylobakatyny III oraz związki pośrednie - Google Patents

Sposób wytwarzania 1,14-węglanu 14ß-hydroksy-10-deacetylobakatyny III oraz związki pośrednie

Info

Publication number: PL200868B1
Authority: PL; Poland
Prior art keywords: carbonate; iii; trichloroacetyl; hydroxy; positions
Prior art date: 2000-08-10

Application number

PL360087A

Other languages

English (en)

Polish (pl)

Other versions

PL360087A1 (en

Inventor

Alessandro Pontiroli

Ezio Bombardelli

Original Assignee

Indena Spa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-08-10

Filing date

2001-07-27

Publication date

2009-02-27

2001-07-27 Application filed by Indena Spa filed Critical Indena Spa

2004-09-06 Publication of PL360087A1 publication Critical patent/PL360087A1/xx

2009-02-27 Publication of PL200868B1 publication Critical patent/PL200868B1/pl

Links

238000000034 method Methods 0.000 title claims abstract description 23
238000002360 preparation method Methods 0.000 title description 10
OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical class O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 title 1
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims abstract description 14
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 3
125000003118 aryl group Chemical group 0.000 claims abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 35
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 25
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 11
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
230000003647 oxidation Effects 0.000 claims description 7
238000007254 oxidation reaction Methods 0.000 claims description 7
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
238000005805 hydroxylation reaction Methods 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
239000007806 chemical reaction intermediate Substances 0.000 claims description 2
AXTYOFUMVKNMLR-UHFFFAOYSA-N dioxobismuth Chemical compound O=[Bi]=O AXTYOFUMVKNMLR-UHFFFAOYSA-N 0.000 claims description 2
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 2
FNZPZCTVRVPPAB-YZSQHPIKSA-N 14beta-Hydroxy-10-deacetylbaccatin III Natural products O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)[C@H](O)[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 FNZPZCTVRVPPAB-YZSQHPIKSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 11
238000005160 1H NMR spectroscopy Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000543 intermediate Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000003480 eluent Substances 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
MEFKFJOEVLUFAY-UHFFFAOYSA-N (2,2,2-trichloroacetyl) 2,2,2-trichloroacetate Chemical compound ClC(Cl)(Cl)C(=O)OC(=O)C(Cl)(Cl)Cl MEFKFJOEVLUFAY-UHFFFAOYSA-N 0.000 description 3
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 3
230000009257 reactivity Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241001330449 Taxus wallichiana Species 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
230000033444 hydroxylation Effects 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical group OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
229940123237 Taxane Drugs 0.000 description 1
241001116498 Taxus baccata Species 0.000 description 1
241000202349 Taxus brevifolia Species 0.000 description 1
235000009065 Taxus cuspidata Nutrition 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000004200 baccatin III derivatives Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
150000004141 diterpene derivatives Chemical class 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
150000002611 lead compounds Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
229940066528 trichloroacetate Drugs 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

PL360087A 2000-08-10 2001-07-27 Sposób wytwarzania 1,14-węglanu 14ß-hydroksy-10-deacetylobakatyny III oraz związki pośrednie PL200868B1 (pl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2000MI001869A IT1318678B1 (it)	2000-08-10	2000-08-10	Procedimento per la preparazione di derivati della baccatina iii.
PCT/EP2001/008730 WO2002012215A1 (en)	2000-08-10	2001-07-27	Process for the preparation of baccatin iii derivatives

Publications (2)

Publication Number	Publication Date
PL360087A1 PL360087A1 (en)	2004-09-06
PL200868B1 true PL200868B1 (pl)	2009-02-27

Family

ID=11445705

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL360087A PL200868B1 (pl)	2000-08-10	2001-07-27	Sposób wytwarzania 1,14-węglanu 14ß-hydroksy-10-deacetylobakatyny III oraz związki pośrednie

Country Status (23)

Country	Link
US (2)	US6828445B2 (ja)
EP (1)	EP1307436B1 (ja)
JP (1)	JP4907043B2 (ja)
KR (1)	KR100853056B1 (ja)
CN (3)	CN100349882C (ja)
AT (1)	ATE277919T1 (ja)
AU (2)	AU8204001A (ja)
CA (1)	CA2418829C (ja)
CZ (1)	CZ302810B6 (ja)
DE (1)	DE60106057T2 (ja)
DK (1)	DK1307436T3 (ja)
ES (1)	ES2228929T3 (ja)
HK (2)	HK1055964A1 (ja)
HU (1)	HU229316B1 (ja)
IL (2)	IL154330A0 (ja)
IT (1)	IT1318678B1 (ja)
NO (1)	NO328124B1 (ja)
PL (1)	PL200868B1 (ja)
PT (1)	PT1307436E (ja)
RU (1)	RU2264394C2 (ja)
SI (1)	SI1307436T1 (ja)
SK (1)	SK286653B6 (ja)
WO (1)	WO2002012215A1 (ja)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1320107B1 (it) *	2000-11-28	2003-11-18	Indena Spa	Procedimento per la preparazione di derivati tassanici.
ITMI20012186A1 (it)	2001-10-19	2003-04-19	Indena Spa	Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato
ITMI20012185A1 (it)	2001-10-19	2003-04-19	Indena Spa	Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato
ITMI20021921A1 (it) *	2002-09-10	2004-03-11	Indena Spa	Funzionalizzazione della posizione 14 dei nuclei tassanici e sintesi di nuovi derivati antitumorali.
US7446126B2 (en) *	2004-10-08	2008-11-04	Indena S.P.A.	Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel
ITMI20050614A1 (it) *	2005-04-12	2006-10-13	Indena Spa	Processo per la purificazione della 10-deacetilbaccatina iii dalla 10-deacetil-2-debenzoil-2-pentenoilbaccatina iii
US20080151139A1 (en) *	2006-12-22	2008-06-26	Itt Manufacturing Enterprises, Inc.	Addressable backlight for LCD panel
DK2080764T3 (da) *	2008-01-18	2012-09-24	Indena Spa	Faste former af ortataxel

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5698712A (en) *	1992-03-06	1997-12-16	Indena S.P.A.	Baccatine III derivatives
IT1275936B1 (it) *	1995-03-17	1997-10-24	Indena Spa	Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni
FR2732341A1 (fr) *	1995-03-27	1996-10-04	Rhone Poulenc Rorer Sa	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
IT1275435B (it) *	1995-05-19	1997-08-07	Indena Spa	Derivati della 10-desacetil-14beta-idrossibaccatina iii,loro metodo di preparazione e formulazioni che li contengono
WO1999037631A1 (en) *	1998-01-26	1999-07-29	Hanmi Pharmaceutical Co., Ltd.	Novel taxaneterpine compounds
IT1308636B1 (it) *	1999-03-02	2002-01-09	Indena Spa	Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii.
ITMI991483A1 (it) *	1999-07-06	2001-01-06	Indena Spa	Derivati tassanici e procedimenti per la loro preparazione
IT1320107B1 (it) *	2000-11-28	2003-11-18	Indena Spa	Procedimento per la preparazione di derivati tassanici.

2000
- 2000-08-10 IT IT2000MI001869A patent/IT1318678B1/it active
2001
- 2001-07-27 HU HU0303832A patent/HU229316B1/hu unknown
- 2001-07-27 RU RU2003103776/04A patent/RU2264394C2/ru active
- 2001-07-27 US US10/343,991 patent/US6828445B2/en not_active Expired - Lifetime
- 2001-07-27 ES ES01960578T patent/ES2228929T3/es not_active Expired - Lifetime
- 2001-07-27 CA CA002418829A patent/CA2418829C/en not_active Expired - Lifetime
- 2001-07-27 EP EP01960578A patent/EP1307436B1/en not_active Expired - Lifetime
- 2001-07-27 DK DK01960578T patent/DK1307436T3/da active
- 2001-07-27 DE DE60106057T patent/DE60106057T2/de not_active Expired - Lifetime
- 2001-07-27 CN CNB2005100873136A patent/CN100349882C/zh not_active Expired - Lifetime
- 2001-07-27 SK SK159-2003A patent/SK286653B6/sk not_active IP Right Cessation
- 2001-07-27 IL IL15433001A patent/IL154330A0/xx active IP Right Grant
- 2001-07-27 PL PL360087A patent/PL200868B1/pl unknown
- 2001-07-27 JP JP2002518192A patent/JP4907043B2/ja not_active Expired - Lifetime
- 2001-07-27 AT AT01960578T patent/ATE277919T1/de active
- 2001-07-27 SI SI200130208T patent/SI1307436T1/xx unknown
- 2001-07-27 WO PCT/EP2001/008730 patent/WO2002012215A1/en active IP Right Grant
- 2001-07-27 CN CNB018138675A patent/CN1254470C/zh not_active Expired - Lifetime
- 2001-07-27 CZ CZ20030365A patent/CZ302810B6/cs not_active IP Right Cessation
- 2001-07-27 AU AU8204001A patent/AU8204001A/xx active Pending
- 2001-07-27 AU AU2001282040A patent/AU2001282040B8/en not_active Expired
- 2001-07-27 PT PT01960578T patent/PT1307436E/pt unknown
- 2001-07-27 CN CNA2007101617507A patent/CN101130528A/zh active Pending
- 2001-07-27 KR KR1020037001790A patent/KR100853056B1/ko active IP Right Grant
2003
- 2003-02-06 IL IL154330A patent/IL154330A/en unknown
- 2003-02-07 NO NO20030609A patent/NO328124B1/no not_active IP Right Cessation
- 2003-11-13 HK HK03108269A patent/HK1055964A1/xx not_active IP Right Cessation
2004
- 2004-10-26 US US10/972,674 patent/US7078538B2/en not_active Expired - Lifetime
2006
- 2006-08-10 HK HK06108866A patent/HK1088325A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
PL360087A1 (en)	2004-09-06
IL154330A0 (en)	2003-09-17
NO20030609D0 (no)	2003-02-07
DE60106057D1 (de)	2004-11-04
CN1254470C (zh)	2006-05-03
ITMI20001869A1 (it)	2002-02-10
RU2264394C2 (ru)	2005-11-20
CA2418829A1 (en)	2002-02-14
EP1307436B1 (en)	2004-09-29
DK1307436T3 (da)	2005-01-31
NO20030609L (no)	2003-02-07
CA2418829C (en)	2009-12-29
US7078538B2 (en)	2006-07-18
HUP0303832A3 (en)	2005-02-28
CZ2003365A3 (cs)	2003-06-18
EP1307436A1 (en)	2003-05-07
HUP0303832A2 (hu)	2004-03-01
ES2228929T3 (es)	2005-04-16
CN100349882C (zh)	2007-11-21
AU2001282040B2 (en)	2005-09-15
CN101130528A (zh)	2008-02-27
ATE277919T1 (de)	2004-10-15
ITMI20001869A0 (it)	2000-08-10
JP4907043B2 (ja)	2012-03-28
SK286653B6 (sk)	2009-03-05
KR20030020454A (ko)	2003-03-08
WO2002012215A1 (en)	2002-02-14
SI1307436T1 (en)	2005-02-28
CN1736995A (zh)	2006-02-22
US6828445B2 (en)	2004-12-07
JP2004505961A (ja)	2004-02-26
NO328124B1 (no)	2009-12-14
CN1446207A (zh)	2003-10-01
US20050113585A1 (en)	2005-05-26
PT1307436E (pt)	2004-11-30
AU8204001A (en)	2002-02-18
CZ302810B6 (cs)	2011-11-23
IL154330A (en)	2006-12-31
DE60106057T2 (de)	2006-02-23
HK1088325A1 (en)	2006-11-03
IT1318678B1 (it)	2003-08-27
US20040014998A1 (en)	2004-01-22
HU229316B1 (en)	2013-10-28
KR100853056B1 (ko)	2008-08-19
HK1055964A1 (en)	2004-01-30
AU2001282040B8 (en)	2006-01-19
SK1592003A3 (en)	2003-07-01

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RU2275365C2 (ru)	2006-04-27	Способ получения производных таксана
PL200868B1 (pl)	2009-02-27	Sposób wytwarzania 1,14-węglanu 14ß-hydroksy-10-deacetylobakatyny III oraz związki pośrednie
AU2001282040A1 (en)	2002-05-16	Process for the preparation of baccatin III derivatives
AU2002229563A1 (en)	2002-08-15	A process for the preparation of taxan derivatives
RU2291866C2 (ru)	2007-01-20	Способ получения 14бета-гидроксибаккатин iii-1,14-карбоната